


The Education of Jacob Frye

by moiraaa



Category: Assassin's Creed
Genre: Attempt at Humor, Disturbing Themes, Explicit Language, Explicit Sexual Content, Light BDSM, M/M, Male Slash, Power Play, Sexual Tension
Language: English
Status: Completed
Published: 2016-05-17
Updated: 2016-05-18
Packaged: 2018-06-09 02:19:04
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 5
Words: 11,591
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6885226
Author URL: https://archiveofourown.org/users/moiraaa/pseuds/moiraaa
Summary: <blockquote class="userstuff">
              <p>Jacob Frye, handsome rogue, man of mystery - invites himself to a party hosted by none other than Crawford Starrick.  His plan?  To take everything Starrick holds dear.  (Un)Fortunately for our hero, even the best laid plans can go awry.  </p><p>---</p><p>Starrick's voice spoke to the deeper, darker parts of Jacob.  Those parts that whispered to him late at night of his fears and failures.  Those parts that affirmed what he had always known about himself but was never brave enough to admit.  </p><p>Those parts that told him he deserved whatever punishment was coming.</p><p>---<br/> </p><p>This takes place towards the beginning of the Assassin's Creed Syndicate story.  I've taken quite a few liberties with the language, so try not to judge too harshly.  </p><p>***Story complete 5/18/16***</p>
            </blockquote>





	1. A Poor Choice in Pants

"Oh, hell..."  

Jacob wiped the excess blood from his coat, causing a spray of droplets to fall onto the face of the crumpled man on the ground.  

"I just had this washed."  He knelt down and started rummaging through the man's pockets.  "Wish I had known you were such a bleeder..." 

Another Friday night, another dead Templar.  He was starting to like London.  

He and his sister had been in London less than a month, and already they had conquered all of Whitechapel.  Well, Greenie had played a part in it, too, he supposed.  A small part.  

_Small part..._   Jacob chuckled to himself as he rifled through the dead man's coat, pocketing the coins and the occasional note before his fingers ran across something thicker.  An envelope.  With a flick of his wrist, it was in his hand.  

"What have we here?"  An invitation. 

 

> _Mr. Crawford Starrick requests the pleasure of Mr. Thompson's company at dinner, on Friday, February 28th, at seven o'clock.  2 Great College Street, Westminster, London  R.S.V.P.  Masks are encouraged._

Starrick.  Crawford Bloody Starrick.  Jacob could hear Evie in his head, _"Don't you dare.  Don't you even think of crossing Starrick so early.  We've only just arrived, and intentionally provoking him would only lead to..."_  

"Yes, blah, blah, think of the Order...blah, blah... not strategically sound...blah."  He leaned down, hooked his arms under Mr. Thompson and drug the corpse back into the shadows.  "Now where's the fun in that sort of thinking?"  

Jacob sat the body up, eyeing his size.  "I believe a change in costume is in order." 

 

 

 Jacob was adjusting his pants just as the carriage rounded a particularly narrow curve.  _Bloody hell..._  He twice hit the top of the carriage with a closed fist, 

"Slow it down some, yeah?"  He readjusted his crotch, muttering to himself, "About lost the family jewels..." 

The pants were a bit too tight for his liking.  Mr. Thompson and he were similar in size, certainly in the shoulders, but down south...  Jacob leaned back, lifting his rear off the seat in an unsuccessful attempt to free his testicles from the vice grip that kept inching up.  _There.  Maybe._   Ugh.  He blew out the air that had been trapped in his lungs just as the carriage hit another bump.  "Ooof."  The evening hadn't even really begun and already he was starting to have second thoughts.  _Where's a good seamstress when you need one?_  

"We're here, sir."  The driver called down to him as the carriage slowed, and Jacob was out the door not a second later.  

"My good man,"  He dropped a few coin into the driver's hand and patted the horse's rear as he made his leave.  He stopped suddenly, turned, and asked, "How do I look?" 

The driver blanched.  "I'm sorry, sir?" 

Jacob gestured to his newly found Templar coat and slowly turned around.  "Do I look presentable?  That is to say, would I turn a few heads?"  He asked with a grin. 

The young man at the reins turned a paler shade of white and nodded.  "Cc..certainly, sir.  Most presentable."  Jacob smiled and turned to leave.  "Though..." 

He stopped mid-step, "Though?" 

"If'n you don't mind me saying, your pants are a little...tight." 

_Damn._  Jacob's head dropped.  "Yes, well,"  He lifted his coat as he walked away, exposing his tightly enclosed buttocks.  "All the better to see my arse with, darling."  

"Cheers!"  The young man laughed as he drove off. 

Jacob smiled to himself as he made his way towards the front gate.  He straightened his arms, triple-checking that his gauntlet was still secure beneath the sleeves.  He reached into Mr. Thompson's coat pocket and secured the invitation. 

_Masks are encouraged._  

Why the hell the Templars were having a masquerade party in the middle of winter was beyond him, but hopefully it would serve as an opportunity to mingle unnoticed.  Well, it would, if he could find the mask.  He started patting down his coat, feeling around for... ah.  He pulled out a thin, porcelain-esque mask, all in black.  He fixed it to his face, pleased to find that it had two small wires attached that managed to tuck in behind his ears, securing it in place.  He brushed his long locks to cover his ears, and voila!  Jacob Frye, handsome rogue, man of mystery. 

"Okay Starrick, ready or not," he whispered.  "Here I come."

 

 

Mr. Starrick's butler stood his ground, eyeing Jacob very carefully; quite clearly not falling for the ruse.  "Sir, you are _not_ Mr. Thompson." 

"Right you are.  Well spotted."  Jacob coughed.  "No, I am here in his stead.  Mr. Thompson fell ill earlier this evening, I'm afraid."  Jacob coolly smiled, adjusting his sleeves.  "My name is..."  _Bollocks.  What the hell is my name?_   _Something churchy..._ "Church..hill.  Christian Churchill.  I am Mr. Thompson's second."  He paused, "I do hope that Mr. Starrick won't be... put out at my arrival." 

The butler just stood there, nonplused.  Silence rang  between them as the butler eyed him up and down a final time.  Jacob raised his eyebrows in silent question. 

A beat... "Certainly not, sir." 

"Wonderful."  Jacob grinned and lightly punched him on the shoulder.  "Now, if there isn't anything else..."  He made his way around the stoic butler, who inched ever-so-slightly to the side.  

"Have a lovely evening, sir." 

Jacob exhaled a deep breath and made his way into the foyer.  The dull roar of the crowd met him as he waltzed into the main room.  _Ah, jackpot._   Jacob found himself in an enormous, dimly lit and extravagantly decorated oak paneled room.  There had to be a hundred Templars; drinking, hobnobbing and complimenting each other on their shared genius.  He should fit right in. 

"Good evening," Jacob drawled.  "Good evening, yes.  Hello."  He slowly danced his way through the crowd, careful to not bump into anyone.  "Wonderful to see you, yes.  Lovely party, isn't it?"  An older, and significantly more drunk, Templar slapped him on the back and shook his hand, right as he took a large swig of champagne.  Jacob excused himself and maneuvered his way to the other side of the room.  Jacob planted himself against a wall, partly hidden by an overly-large fern.  

He eavesdropped on as many conversations as he could, listening for any mention of his or Evie's name, but to no avail.  Slightly crestfallen, he did perk up a bit listening to one female Templar agonizing over the Rooks sudden appearance, so that helped lift his spirits a bit.  He watched the crowd intently, searching for anyone he might recognize.  Blasted masks.  Though helpful in his own deception, it made it damn near impossible for him to identify anyone.  _Where was Starrick, that old bastard..?_   He was about to change locations when a voice boomed over the masses. 

"Good evening, everyone."  

The Templars turned in unison, and there, on the stairs with his arms raised in welcome, was Crawford Starrick, followed very closely by Lucy Thorne.  The crowd erupted into applause.  Starrick made his way down, taking one leisurely step at a time till he was about midway down the impressive staircase.  The crowd quieted in time with his lowering hands, till there was only the sound of clinking glasses and bated breaths.  Jacob crossed his arms, a faint smile on his face.  The amount of control Starrick had over his people was impressive.  It took Jacob at least five to ten tries to finally get the small amount of his Rooks to shut the bloody hell up. 

Starrick clasped his hands together.  "Friends, compatriots, welcome.  It warms my heart to see you all here."  He grimaced a smile, gesturing to the crowd.  "We are here tonight to celebrate.  Not only our accomplishments, of which there are many," he bowed his head in acknowledgment of his lieutenants.  "But we also celebrate our future, which has never looked so bright."  Another cheer from the crowd.  "London, the high jewel of the world's crown, is in a golden age.  Through sacrifice, leadership, and faith, we have brought our London out of the darkness.  Never again will we let this jewel slip through our fingers and into the dirt of the common people."  Another roar from the crowd.  "No, we will lead them, and in turn, the world, into the light." 

Lucy Thorne raised her glass and spoke, "May the Father of Understanding guide us."  Though it was small, Jacob spied a slight falter in Starrick's smile, and a quick glance to his second in command.  _Oooh... I_ _think she took his line_ , he laughed to himself.  

Hundreds of voices replied in unison, toasting their leaders.  "May the Father of Understanding guide us." 

"My friends, now is not the time for speeches."  Starrick pulled in the reins from Ms. Thorne.  "Now is the time to celebrate!"  Another raucous cheer from the crowd of Templars.  "Dinner will be served in the dining room."  And with a sweeping gesture from Starrick, the doors to the dining room swung open, and the crowd started to make its way in. 

Jacob took his cue and slinked around the corner towards the kitchen, but not before observing a very cross Starrick having words with his second in command.  

"I'd hate to be Ms. Thorne right now," Jacob laughed and moved around the corner.  Mingling is one thing, but sitting down for a ten course meal next to God knows which Templar could be problematic.  Not only would he be risking discovery, but good God - how terribly dull.  One can fake rapt attention for only so long.  

The kitchen was brightly lit and immaculate, with every food of every type hot and ready to be served.  After making sure he was alone, Jacob weaved his way around the tables, picking a piece of chicken here, a grape there, and popping them into his mouth.  

"Mmmmf, very nice," licking his fingers appreciatively.  The chatter of the kitchen staff was getting louder, so Jacob grabbed a drumstick, some fruit and a handful of rolls and ducked into a curtained closet.  

"Quickly now girls, quickly - we need to get the first course out.  Sarah, grab that ladle and follow me."  The staff worked quickly and diligently around where Jacob was hiding, but he didn't mind.  He could use the break.  Having not eaten much at all today, Jacob silently noshed while the kitchen whirled with activity.  

Suddenly, the noise stopped, and the hair on the back of Jacob's neck stood on end.  The kitchen was eerily quiet, save the booted footsteps walking his way.  His eagle vision showed a red figure just outside his curtain.  Jacob popped the last strawberry into his mouth and readied his gauntlet.  

Then, just as he was ready to strike, the traitorous strawberry fell from his lips and rolled out from under the curtain. 

_Dammit._  

A set of very large and very well manicured fingers leaned over and picked up the half-eaten strawberry.  A darkly bemused voice called out, "I think you dropped something." 

Jacob steadied his gauntlet.  To be clear, he wasn't afraid of creating a few bodies.  However, he was surrounded by more Templars than he could count, and a kitchen full of screaming cooks wouldn't help his situation any.  The voice didn't sound angry, so perhaps there was a chance he could charm his way out of this mess.  He rolled his shoulders and readied his smile.  

"Indeed, sir."  He pulled back the curtain.  "I did, in fact, drop my..."  Jacob's mouth went dry; it was Starrick.

"...fruit?"  Starrick replied, a small smile pulling at the corner of his lips.  

"No one's called me that in years."  Jacob's look of surprise quickly melted into a smile.  "But you can call me Jacob..Christian.  Er, Jacob Christian Churchill, at your service"  He inwardly winced.

Crawford Starrick stared at him.  The small look of amusement tugged ever-so-slightly more at this lips, and he stuck out his hand.  "Crawford Starrick."  Jacob took his hand and shook it.  "Pleasure."  

The heat that radiated off of Starrick's hand was intense, which surprised Jacob.  He had always figured Starrick for the cold, clammy type. 

Starrick pulled his hand away.  "Now, may I ask, what were you doing hiding in my kitchen?"  

"Ah, yes.  That."  Jacob shrugged.  "Prefer to eat alone.  I'm not so good with crowds." 

Starrick furrowed his brow and nodded at that; he moved slowly over to the nearby table and leaned against it, pouring himself some tea. 

"I find myself seeking solitude most times, as well."  He crossed his feet and tucked an arm under his opposite elbow.  "Why are you here?" 

Jacob smiled, "I don't suppose you have a Jacob Christian Churchill on your guest list." 

Starrick slowly shook his head. "No, I don't."  He put down the cup, then took a step closer to Jacob. 

"Of course not - why would you?"  Jacob willed himself not to move.  Every fiber of his being screamed at him to slit Starrick's throat and run.  

Starrick agreed, "Why would I?"  And took another step closer.  There was a predatory look in his eyes. 

Jacob's pulse quickened.  "I wasn't invited."  

"No, you weren't."  Starrick stopped walking, maybe a foot away from Jacob.  He paused.

"I know why you're here."   

_Here we go._   Jacob's smile got bigger as his eyes narrowed.  "And why is that?"  He squared his shoulders, meeting Starrick's gaze. 

Starrick slowly lifted his hand to Jacob's face and wiped away the last bit of strawberry from his mouth.  

"Roth sent you."  He then proceeded to suck the remnants off his thumb, never breaking eye contact with Jacob. 

The Assassin tried to ignore the electric sting left behind by Starrick's touch.  _Roth?  Who in the hell is Roth?_     Jacob, ever the smooth operator, tried his best to not give away his confusion.  

"What gave it away?"  

That evoked a small chuckle from Starrick.  "You.  You gave it away."  He gestured to Jacob, drinking in the young Assassin with his eyes.  "I've known Roth a long time.  And he... knows my type."  His eyes connected with Jacob's once more.  

"Besides," Starrick cocked his head and looked down.  "Those pants leave nothing to the imagination."

A glimmer of surprise flashed across Jacob's face.  "I'm flattered."     

Another small smirk crept onto Starrick's face.  "You should be."  He turned to leave.  "My private quarters are the third door on the left from the top of the stairs."  Starrick looked over his shoulder, "I'll see you there in two hours time."  He nodded, then leisurely walked out of the kitchen. 

"Indeed you will, Mr. Starrick."


	2. Adding Insult to Injury

Jacob stood in the kitchen a long while after Starrick had left. 

 _What just happened?  What did I just agree to?_ Jacob pulled at his crotch. _Merciful Lord, why are my pants so much tighter?_   He lightly hit the back of his head against the wall in frustration and closed his eyes.  

 _He was there.  Starrick was RIGHT THERE, and I didn't kill him._   The Assassin blew out the remaining breath in his lungs and sank against the wall.  

"And who the hell is _Roth_?"  He asked no one in particular.  Jacob made a mental note to check the board when he got back to the train.  _If_ he got back to the train. 

 _Cant think like that_ , he chastised himself _.  Nothing's changed but the timeline.  Starrick now expects to see me in his private quarter._   _He's made my job easy._   Jacob grinned at the thought.  _I'll sneak in, collect as much intelligence as I can, and wait for him in his room._  

Jacob slapped his knees, jumped up and headed out the door, but not before grabbing a few strawberries for the trip.

 

 

While focusing on a single task was never Jacob's strong suit, he found this evening's task infinitely more arduous than normal.  Getting to Starrick's chambers was easy enough, as was picking the lock to his office and private study.  However, successfully investigating the many drawers and cabinets throughout proved...difficult. 

His mind kept wandering. 

Wandering back to those steely gray eyes and how they looked at him.  Starrick saw him, really _saw_ him.  It was unnerving.  Certainly, Crawford wasn't particularly bad to look at, either.  He wasn't as handsome as Jacob, of course, but he had this...way about him.  Every thought was calculated.  Every move precise.  And to have a man who only wanted the best want you...well, it did boost the ego a bit.    

The tightness in Jacob's stomach returned, and he had to wave away any wandering thoughts of Starrick.  He _had_ to get through all these blasted files.  

He searched through stacks and stacks of papers, taking note of shipments, dates, warehouse addresses, it was a good start.  But then, after a brief struggle with a particularly difficult lock... 

 _Holy..._  

There before him was every piece of information the Templars had on the pieces of Eden there in England, and in every other part of the empire.  Charts, maps, sketches, files and files of data, obviously collected over generations.  The loss of this information would be devastating, not only to the Templars, but to Starrick in particular.  

_It would end him._

Jacob was elated. 

There was far too much there to take back with him, so Jacob took as many detailed notes as he could.  He drew the maps, haphazardly redrew sketches, did everything he could to compile as much information into as little a space as possible.  Everything went into his coat pocket when he was finished.   

Jacob stood a little taller, his strides were a little longer, and his chest, if possible, puffed out a little more than normal.  He quietly skipped around the office, closing drawers and stowing papers.  To say that Jacob was proud of himself was an understatement.  

_I could leave right now, and it would be as good as killing him._

"But where's the fun in that?"  He smirked to himself.  This could be the last time he'd have the chance to get this close to Starrick without Starrick knowing all that he's done.  Without Starrick knowing who _he_ is.  

Jacob relished the idea of Starrick wanting him.  The thought of having the Grand Master writhing beneath him was intoxicating.  He could picture it; Starrick's face caught in a moment of agonizing pleasure, his body pliable and open to the Assassin's every whim.  He would take him.  All of him.  Take everything Starrick had. 

_Let's add a little insult to injury._

 

 

Jacob opened the door to Starrick's room, checked to see if the coast was clear, and then clicked the door shut behind him.  He scanned the room, appreciating Crawford's taste for the finer things.  

His room, much like the rest of his house, was paneled all in oak.  Rich colors and textures were everywhere.  There was an ornate dresser and mirror set to the side with a chair that looked more like a small throne than the stool one would normally use.  There was a set of velveteen round back armchairs to the right with bookshelves all around.  The centerpiece of the room, however, was the four poster bed on the far side of the room.  It was enormous with curtains and spindles and the like.  A bed fit for a king.  

 _Or a man who thinks he's a king._   He snorted. 

Jacob took off his coat and folded it on the back of the chair by the fireplace.  He made to sit down but stopped, eying the gauntlet on his arm.  _Well, shit... can't have this on, less I give the whole game away._   Evie's voice in the back of his head chastised him for the very thought of taking the gauntlet off when he was this deep into the lion's den.  He agreed that the idea was risky, but the reward was more than worth it.  He unbuckled the fasteners attaching it to his arm and placed it within the folds of his coat.  

Just then the door clicked open. 

" Mr. Churchill,"  Crawford Starrick walked in, closing the door behind him.  He hung his coat on the hat stand by the door and turned to face Jacob.  "I see you've made yourself at home."  His tone was formal.                                      

Jacob was sitting on the arm of the chair with his legs crossed at the ankles.  "Indeed I have, Mr. Starrick."  He put on his most charming smile as he gestured to the room.  "Quite a place to call home." 

"Indeed it is."  Starrick approached Jacob, his hands in his pockets.  He watched Jacob carefully, his look was... difficult to read.  "I'm pleased you had the good sense to not keep me waiting." 

Jacob smiled wolfishly and looked up at Starrick through veiled eyes, uncrossing  and re-crossing his legs.  "I've been told I can be _very_ pleasing."   Starrick's feet were on either side of Jacob's legs now.  

"Hmmm," was all that Starrick replied, though there was a glint in his eye that hadn't been there before.  Taking his time, he bent at the waist till they were eye level.  He then raised his hand, pressed it to Jacob's face, and carefully slid off the mask.  "You don't need this anymore." 

The Grand Master stayed eye level with the Assassin for what seemed like an eternity.  Jacob met his gaze, but he was damned if he couldn't tell if Starrick was seducing or studying him.  Jacob wet his lips, angled his head and leaned in for a kiss.  

Starrick stood, leaving Jacob's face and lips inches away from his crotch for a moment before turning and walking towards the other side of the room.  "Hang your coat on the rack by the door."  

Jacob was floored.  Never before had his advances been so... ignored.  Starrick had said something...

"Sorry?"                                                                                                                                                              

"By the door.  There's a rack.  Hang your coat on it."  Crawford finished unbuttoning his vest and hung it on a hanger in his armoire.  "You may leave your boots there, as well."  He started undoing his cufflinks. 

Jacob made a face.  "Yes, sir."  

He softly chuckled as he grabbed his coat, almost forgetting about the gauntlet hidden within its folds.  _Damn._   He kept his back to Crawford as he made his way towards the door.  He hung the coat, concealing the gauntlet behind it, bringing it down with him to the floor as he loosened his boot.  _Curtains._   He stealthily hid the weapon behind the curtains and went back to taking off his other boot, followed shortly by his socks. 

He stood, resisting the urge to adjust his inseam.  "Any other articles of clothing I can take off for you, Mr. Starrick?"  

Crawford turned, raised an eyebrow, and allowed another half-smile to tug at his lips.  "No, that will be all... for now."  He gestured to the miniature throne by the dresser.  "Please, sit." 

Jacob nodded his head with a smile and sauntered his way over.  In a quick movement, he adjusted the chair and laid back.  He watched as Starrick undid his necktie. 

Adept fingers quickly undid the complex knot, sliding purple silk across and under itself.  Crawford didn't look down to watch his hands, or to make sure he didn't make a mistake; he only looked at Jacob.  

"So, Mr. Churchill..." 

"Jacob, please." 

Starrick nodded, "Jacob.  How well acquainted are you with Roth?"  

"Not very."  Jacob admitted.  _Or at all_ , he thought to himself.  Starrick was in the process of shrugging off his suspenders, which fell to hang on either side of his thighs. 

"That's surprising."  Crawford began unbuttoning his shirt.  His fingers pushed the ivory circles through their respective holes with a slow rhythm.  "Seeing as he felt well enough acquainted with you to send you to me."  He shrugged off the white linen, catching it as it fell behind him, and placed it neatly on its hanger.  

He shrugged.  "Perhaps I'm just that much more transparent..."  Jacob trailed off as Starrick's movements caught his attention. 

Though Crawford was careful not to mess up his well-coiffed hair, a few strays managed to go rogue and fell into his face as he pulled the undershirt over his head.  His abdomen was rippled, thick and strong.  Not as defined as Jacob's, the Assassin noted, but still... for as much time behind a desk as he assumed Starrick spent, this was... surprising.  His skin was smooth, hairless, save for the black trail that started just below his belly and went down... 

 _Oh..._  

Starrick caught him staring.  "Transparent.."  His voice took an amused tone.  "Between your face and your..."  He glanced at Jacob's crotch.  "...pants, yes.  I would say so."  

Jacob's dick throbbed involuntarily at Starrick's gaze, and he sucked in the air with a soft hiss. 

Starrick then began to unbutton his pants.  He pushed them, slowly, over his buttocks where they fell to the floor. He stepped out of them and again, like his shirt, hung them neatly on their respective hanger.  His socks came off with a quick tug on each foot, and were quickly tossed to the side.  

The thin material of his drawers was the only barrier that separated all of Starrick from Jacob's intentions. 

 _Holy hell._   Jacob's pants were impossibly tight.  He sat up, trying to change positions.  _I am going to burn these blasted things..._ That was when Starrick turned and walked toward him. 

"Unbutton your shirt." 

"I thought you'd never ask,"  mumbled the Assassin, who was more than happy to comply.  His fingers flew across the ivory buttons, un-tucking his shirt as he went.  Jacob rolled his shoulders, untangling his arms till the shirt lay crumpled on the seat behind him.  He could feel Starrick's eyes on him.  

"No undershirt?"  It wasn't a question but a judgment.  

Jacob felt a flicker of anger.  "We can't all put on a twenty minute show to undress, Mr. Starrick."  His tone was impertinent.  "Or we'd be here all night."  

A blinding white-hot pain flashed across Jacob's cheek and his head flung to the side.  The world went hazy.  He couldn't think.  Jacob felt the blood from his busted lip trickle down his chin. 

 _That bastard just fucking hit me._   

The Assassin snapped his head back towards Starrick, his eyes blazing.  He was halfway off the chair when Starrick's knee landed between his thighs.  Crawford was on him, pushing him back into the chair and invading Jacob's mouth with his tongue.  The kiss was brutal, sending shockwaves through Jacob's body.  Starrick broke the kiss, pulling Jacob's head back by his hair.  

"You talk too much."  Starrick's voice was soft.  "I know of a better use for that mouth."  With his knee still firmly planted against Jacob's crotch, Starrick stood upright.  

Head still spinning, Jacob watched as Starrick's hand slid over his own stomach and into his drawers.  His eyes widened when Crawford grasped the bulge beneath the thin layer of cloth, pulling and kneading it to life.  Starrick's eyes closed and he let out a low moan.  Finally, the Grand Master unbuttoned his drawers and they fell to the floor. 

Crawford Starrick looked exquisite standing naked before Jacob.  The candlelight cast dancing shadows on his bare skin, enhancing the already impressive lines of his muscles.  Starrick was unhurried as he tugged and at his half-erect cock, letting it bounce and bob dangerously close to Jacob's face.  

"Come closer."  Starrick's voice was deep and dark and broke Jacob out of his stupor, the sting of his cheek long forgotten.  He scooted forward on the chair, forcing his already sensitive groin into Starrick's knee.   

"Open your mouth."  With his eyes directed at the floor, Jacob wet his lips and tentatively opened his mouth.  His stomach was flip-flopping with nervous energy. 

After what felt like an eternity, Starrick's index finger slid over his tongue.  With a hungry groan, Jacob  started to suck.  He ran his tongue along the sides, tasting his skin, extracting a moan from Starrick. 

"Good."  

He pushed another finger into Jacob's mouth, and Jacob was only too willing to comply.  Starrick slowly started pulling and pushing them in and out of the young Assassin's mouth.  Jacob raised his eyes to find Starrick massaging his cock in time with the rhythm.  A surprised moan reverberated in his chest, and he began to suck harder. 

"Less teeth, use your lips."  Starrick's command was less forceful, his breath had become ragged.  Jacob obeyed and covered his teeth with his lips, still sucking with as much fervor as before.  Starrick chuckled and ran his fingers through Jacob's thick head of hair. 

"So eager to please."  

Starrick pulled his fingers from the young man's greedy lips.  He gave his cock a final squeeze and presented it to Jacob, letting it dangle in front of his face before filling his mouth once more.  Jacob was unready for its size and had to widen his mouth considerably.  Starrick didn't give him much time to adjust, and before long he was thrusting, forcing his length into Jacob's mouth.  

Starrick's hand gripped the back of the Assassin's head tightly, guiding him.  A muffled plea reverberated in Jacob's throat, causing Starrick to moan loudly, increasing his speed. 

Jacob's head was racing but there were no conscious thoughts.  He was in sensory overload.  The taste of Starrick was salty and pungent and everywhere.  His dick was on fire, ready to explode out of his pants, and yet he clung closer to Starrick, rocking against his thigh.  He couldn't breathe.  He couldn't think.  He could only feel, and it felt amazing.  

He opened his eyes, and their gazes locked.  Starrick rolled his head back and a dark moan escaped his lips.  His pace quickened along with his breathing.  Jacob felt like the hair on the back of his head was going to be ripped out at the roots.  His grip on Starrick's cock quickened, banging into his own lips.  Suddenly, the back of his throat was on fire.  His panicked cry was muffled by the roar of Starrick's orgasm.  Crawford's thrusts slowed and his grip lessened, but his posture never wavered.  He remained upright till he was finished.  

Jacob swallowed as Starrick slowly pulled out of his mouth.   He staggered back a bit, resting his weight against the armoire.  Jacob slunk back in his chair, wiping his mouth and covering his face with the palms of his hands.  They smelled of sweat and musk.  

"Impressive..."  Starrick had recovered his voice.  "...for your first time." 

Jacob's head shot up, probably too quickly, then fell down again.  He laughed as he sighed,  "That obvious?"  There was a guarded look in his eyes.  

"Transparent," said Starrick with a tired laugh.  

"Oh no, don't tell me you've developed a sense of humor."  Jacob swooned, "I don't think my delicate sensibilities could take the shock." 

Starrick stiffened; the relaxed moment was gone.  

"What _can_ you take, Jacob?"  He lifted his body away from the armoire and moved closer.  "I'm curious." 

Another wolfish grin graced Jacob's lips as he cocked his head to the side.  His hand moved down to his crotch.  "Get me out of these pants and I'll show you."  He gripped his bulge as an invitation to Starrick.  

Crawford's eyes were unreadable.  He stood there a moment more, then slowly moved around behind Jacob, almost as if he were stalking him.  He leaned in close to the Assassin's ear and breathed, "Would you like to play a game?"


	3. You Won't Win

Jacob raised an inquisitive eyebrow.  "Possibly.  What are the stakes?" 

Starrick leaned in closer.  "Above or below.  Give or receive."  His breath was hot on Jacob's neck.  "Winner decides the other's fate." 

Jacob's eyes closed and his mind flashed to an earlier thought.  The image of having Starrick writhing beneath him; his distinguished face caught in a moment of agonizing pleasure.  He bit his lip and opened his eyes. 

"And the rules?"  

"You can't climax..." Starrick's mouth closed around Jacob's earlobe.  "...until I say you can."  He bit down, eliciting a gasp from the young Assassin.  

Jacob growled, "Deal."  In a movement faster than Crawford was expecting, Jacob reached around, grabbed Starrick by the back of his head and pulled him into a fierce kiss.  Jacob's jaw was taught, working his tongue furiously into the older man's mouth.  Starrick allowed it, but only for a moment and then he pulled away.  

"I wasn't finished."  There was an edge to Starrick's voice. 

"Neither was I," the Assassin objected.  His face was flushed.  

"You will do what I say, how I say.  No exceptions."  He moved around to face Jacob.  "Now stand." 

Jacob complied, but his tone was mocking.  "Yes, m'lord." He saluted.  

That earned him another blow from the back of Starrick's hand.  

With a yell, Jacob was knocked back into his chair.  He was back up on his feet in a blink, his arms drawn back and ready to return the favor.  He swung.  Starrick dodged and landed another good hit to Jacob's side.  

In a move faster than Jacob was expecting, Starrick wrapped his body around and behind Jacob's; his right arm enclosed around the Assassin's neck, while his left hand followed his body down and gripped onto Jacob's crotch.  The Assassin's throat was trapped in between Crawford's forearm and bicep.  Starrick squeezed. 

"So impertinent..."  Starrick sighed.  "Like a child."  Jacob struggled under his grip, trying to throw off Starrick's hold on him.  All of his thrashing was causing his groin to move against Starrick's hand, adding another level to his frustration.  Jacob growled angrily.  

"Are you done?"  Crawford's tone was almost bored. 

When Jacob didn't answer, Starrick let his hand do the asking, running his fingers along the outline of Jacob's cock.  The young Assassin involuntarily moaned and his knees weakened.  His body momentarily sagged against Starrick's as the Grand Master strengthened his grip on Jacob's neck.  

He couldn't breathe.

 _Nonononono_  

The world started to spin.  

 _No..._  

The last thing Jacob heard before he blacked out was Crawford's voice in his ear.  

"Don't fight me," he whispered.  "You won't win." 

 

 

The first thing Jacob could feel was his throat.  The throbbing, fiery pain radiated from the bottom of his chin all the way down to his collar bone.  Jacob coughed and immediately winced from the pain.  All in all, it was a decidedly terrible way to wake up.  

It was when he went to check his body for more injuries that he discovered he was in manacles - his arms were raised out and above his head.  He followed the chains with his eyes.  They went far up into the ceiling, into the shadows.  In fact, the only lit area in the room was the large circle of light he found himself in, illuminated by a huge chandelier far above him.  The edges of the room were a dark, inky blackness.  He struggled against his chains to no avail.  His ankles were also encased in manacles, but he still had enough slack to kick if he had to.  

 _Well there's a slice of good news._  

As he kicked into the air, a large realization hit him in the thigh.  His pants were gone. 

 _Of course, NOW they're gone..._  

A noise to his left startled him.  A door had just slid open in the wall; the butler that had earlier tried to block his entry was now wheeling in a tea cart.  Jacob had just enough time to raise a leg to cover himself in a pathetic attempt at modesty. 

"Hey!"  Jacob coughed again, his voice was shredded.  Still, the butler heard him and raised his head.  

"Yes, remember me?  From earlier?  You almost didn't let me in."  He coughed again, straining his voice.  "Honestly, all things being equal, I really wish you had stuck to your guns on that..."  He chuckled and then shook his head, "Never mind.  Can you..." 

"He won't help you, Jacob."  A voice called out from behind him.  Jacob twisted his head around enough to see a robed Starrick emerging from the shadows.  "Thank you, Barnes, that will be all."  

The butler bowed and, with one final look at Jacob, he took his leave. 

The Assassin was livid.  He fought against his restraints, rattling the chains. "What are you playing at, Starrick... " He was seething.  

"A game, remember?"  Starrick's smile was patronizing.  "I distinctly recall you agreeing to play by my rules." 

"Fuck your rules."  The words spat out of Jacob's mouth like bile.   

Starrick chuckled softly and made his way over to Jacob, running a warm hand across the Assassin's chest before taking hold of one of the manacles.  "This," gesturing to the manacle, "is your fault, Jacob.  Had you not attempted to strike me, we could've avoided this unpleasantness."  

He turned and walked toward the tea cart where he poured a glass of wine.  "Don't think me unkind." Starrick held the glass to Jacob's lips, as a sort of peace offering.  "Your neck injury was regrettable."  

Jacob ignored the wine, preferring instead to bore holes into the Starrick's forehead with his eyes.  Crawford shrugged slightly.  "It's not poisoned, I can assure you."  He took a slow drink, offering it back to Jacob.  The assassin still made no attempt to drink it. 

"Tsk tsk.." Starrick shook his head and put the glass back down on the cart.  "I may have misjudged you."  He raised his hand and gently ran it across Jacob's cheek.  "I assumed you understood that my...desires... are of a particular nature."  He ran his hand down the Assassin's abdomen as he maneuvered his way around and behind Jacob.  

"I long for control in all things," his voice was silky smooth.  "I demand order in a world of chaos,"  he ran both of his hands down Jacob's sides, pushing them over his hipbones, and pulling himself against Jacob's back.  

Crawford whispered into his ear, "And you, my Jacob, are chaos incarnate."  His fingers grazed Jacob's pubic hair, making the Assassin exhale sharply.  "You are the darkness to my light."  Crawford's hands moved along either side of Jacob's enlarged cock, eliciting another moan.  "Can't you feel it?" 

Jacob's eyes had rolled into the back of his head.  Rage and desire battled for his heart as Starrick's words washed over him.   He was burning with fire - anger, passion... they were one and the same for him.  His cock was starting to throb, adding fuel to the inferno that was already overtaking him. 

Starrick's mouth was on his shoulder, licking and biting where his shoulder met his neck.  Jacob cried out; the pain, and surprisingly, the pleasure of it, was excruciating.  Jacob shook his head and let out a frustrated and desperate howl.     

"Let me rule you, Jacob."  Starrick's breath was hot on his neck.  "Just for one night.  Let me own you."  His voice was low and lustful, full of dark promises.  

 _Fuck._  

With a quiet resignation, the rage that held Jacob's body rigid lifted its grip, and he sank back against his captor.  For as hard as he tried to dismiss it, the electricity he felt at Starrick's touch won out.  Jacob yearned for more, and he hated himself for it. 

Starrick's voice spoke to the deeper, darker parts of Jacob.  Those parts that whispered to him late at night of his fears and failures.  Those parts that affirmed what he had always known about himself but was never brave enough to admit.  

Those parts that told him he deserved whatever punishment was coming.     

 _God help me._  

Jacob's reluctant sign of submission brought a triumphant smirk to Starrick's face.  He let out a predatory growl as he bit down on Jacob's ear lobe.  "I want to hear you say it." 

Jacob rested his head back on Starrick's shoulder and looked up at the chains that held him.  

"I'm yours... for tonight."  He squeezed his eyes shut and prayed that he hadn't just damned himself. 

Crawford was pleased.  He leaned in close. "Very good."  Though his voice was soft, it brought little comfort to Jacob.  Starrick gently ran his fingers through his hair and lifted Jacob's head off his shoulder.  He made his way over to the tea cart and poured another glass of wine. 

Starrick offered the wine once more.  "For your throat."  Jacob was hesitant, but sniffed the glass.  He caught whiffs of sweet herbs and something medicinal.  His instincts told him to stay away, but the pain in his throat won out.  He took a few small sips, and then opened his throat to the rest of the glass.  It was bitter, not at all the sweet herbs its aroma advertised.  Still, it felt good going down his throat, numbing it as it went down.  

Jacob felt the wine enter his bloodstream, dulling his senses and the pain in his neck.  He felt good.  Too good. 

"Laudanum?"   Jacob blinked hard, trying to focus on Starrick.  

"It's a mild dose," Starrick was moving outside of Jacob's eye line.  "Just enough to numb some pain."  He could hear chains being moved.  

Jacob laughed, "So, you had to drug me before you released me?"  His head felt loose on his neck.  "Afraid I might fight back?"  

He heard the chains once more, and then, suddenly, his legs were pulled far apart and the grip on his arms was tightened.  

"Not quite."  Jacob could hear the smile in Starrick's voice.  Apparently Crawford wasn't planning on releasing him anytime soon. 

The Grand Master made his way out of the shadows, dragging a chair behind him before finally sitting it down in the middle of the room.  Standing behind the chair, Starrick loosened the sash of his robe, letting it fall open.  He placed his hands on the back and leaned forward, studying Jacob.  He remained there for a time, admiring his work. 

"I quite like you like this."  Starrick slowly moved out from behind the chair, his robe blowing more open as he walked.  Jacob watched him with hungry eyes.  Crawford stood before Jacob, running his fingers over the Assassin's stomach, tracing the outline of his muscles.  Jacob closed his eyes and took in a breath.  "So powerful, and yet, so powerless."   

He ran his hand down, following Jacob's trail of hair and letting his fingertips lead him around the base of Jacob's cock, tracing the veins as it bounced under his touch.  Jacob groaned, his hips involuntarily thrust forward into Starrick's hand.  

"Tsk, tsk.. so eager."  Starrick wrapped his hand around Jacob's half-erect cock, sliding up and down its length at a measured pace.   

"Oh...God..."  Jacob moaned loudly. He was starved, craving human touch.  After the night he'd had, this was long overdue.  

Starrick kept his pace steady, studying Jacob's every movement.  He moved his free hand beneath the Assassin; using his fingers, he began to massage the area just behind his balls.  Jacob's eyes popped open and immediately rolled into the back of his head.  A louder, more ferocious moan broke through his clenched teeth.  

It felt so good.  Jacob's breathing quickened as he felt the tightness in his stomach flow down and into his balls.  He was close... 

Jacob whined as Starrick took away his hand.  

"Did I say you could finish?"  Starrick's tone was coy. 

Jacob held back the urge to roll his eyes.  "N..no.  You did not."  Though he ached for release, he tried to keep his tone civil.  He knew that Starrick could keep this going for as long as he wanted - no point in antagonizing his captor. 

"Very good."  Starrick smiled.  "Remember the wager.  If you climax before I say you can, then I decide how and where to ravage you."  He grabbed Jacob's cock and squeezed, evoking a pained gasp from the Assassin.  

"But if I last..."  Jacob managed a smirk.  His gaze was hungry.  

"If, indeed."  Starrick cocked an eyebrow.  He took a leather strap out of his pocket and held it up to Jacob's face.  "This will help."  It was a long strip of leather with two metal studs on one end and several small holes at the other.  Jacob was immediately apprehensive about what Starrick planned to do with it.  

As if Starrick was reading his mind, he smirked and held it below Jacob's ball sack.  With skillful hands, he quickly wrapped it around the top of Jacob's cock and secured the two studs within the holes, making sure it was good and tight.  The miniature belt held Jacob's cock and balls in an almost vice-like grip out and away from his body.  

"Holy hell..."  

Jacob's body slowly loosened as he got more accustomed to the feeling.  His dick was starting to turn a slightly darker shade of pink and he could feel his pulse lightly emanating from it.  

He looked at Starrick incredulously, "This is supposed to help me?" 

A smirk tugged at Crawford's lips, "Let's find out."  

Starrick slowly dropped to his knees, maintaining eye contact the whole trip down.  He took Jacob's erection in his hands and ran his tongue along its length, causing Jacob to groan.  He took his time running his tongue over the head, applying pressure along the slit.  Jacob pulled desperately against his chains, growling in pleasure.  

Starrick sucked greedily at Jacob's cock, running his hand along the length before opening his throat - taking all of Jacob into his mouth.  Crawford moaned; the vibrations sending Jacob into a frenzy of half-moaned curses. 

Jacob was lost in the sensations, which were made all the more powerful from the leather wrapped around him.  The pleasure was intense, but it wasn't building like before.  An encouraging thought appeared in his mind. 

 _I might win._  

A loud laugh escaped his lips and quickly turned into a growl of satisfaction.  Crawford slowed  to a stop, giving a final lick before standing back up.  

"Your restraint is admirable."  Starrick wiped his mouth with the back of his hand.  "But that was just the first of many attempts."  He walked over to the tea cart and dipped his hands in the water basin, giving them a thorough cleaning.  Satisfied, he dried them and walked back over carrying a glass jar filled with what looked like olive oil.  

Jacob watched him pour some of the oil onto his fingers and rub them together.  Starrick's eyes met Jacob's, and there was a hint of...something.  Mischief?  Knowing?  It unnerved him, and he shifted in his manacles.  Starrick moved backwards and he was gone - into the shadows.  

There was nothing but silence. 

"What are you doing?"  Jacob's voice was unsteady. 

There was more silence, till a low voice spoke from right behind him.

"I'm going to introduce you to your demons." 


	4. The Game

The Assassin jumped a little when Starrick whispered in his ear.  "This might be a little...startling."  Suddenly, there was a slick hand on his ass, squeezing and kneading it.  The hand crept inwards, down into his crack, then a warm, wet finger started to massage the opening.  

Jacob held back a moan.  Slowly, Starrick pushed a finger in.  Jacob tensed and a surprised noise leapt from his mouth.  

"Relax," Starrick made a hushing sound and kept pushing.  "Tensing only makes it worse."  As Jacob willed himself to relax, Crawford began rotating his finger - stretching him out.  Jacob couldn't get comfortable.  A flush came to his cheeks and a feeling of embarrassment filled his chest, making it hard to breathe. 

"I can't..."  His voice stammered.  

"Jacob," Starrick's tone was impatient.  "Our agreement..."  Jacob's head dropped, a shaky sigh escaping.  

After a moment, Crawford pushed in another finger and continued the stretching.  It was an intense pressure, and Jacob kept having to remind himself to stay relaxed.  He started breathing in quick breaths, trying to distract himself from the feelings that were building up inside of him.    

_What would Evie say if she could see you like this?_  

Jacob willed away the dark voices in his head.  His eyes felt hot, like they would start spilling tears any moment.  He took a big breath.  

Starrick pushed his fingers in a little deeper, searching till he found the spot he was looking for.  He then began to massage the firm nodule in slow circles.  Soon... 

"Oh my God."  Starrick smirked as Jacob's voice got a little higher.  "Oh, oh... oh God.  Oh GOD..."  Crawford kept massaging, keeping the rhythm steady, and eliciting more vulgar expressions from Jacob. 

What had started as just pressure turned into a building pleasure that was becoming more intense than anything Jacob had experienced before.  He was babbling, speaking in tongues, not even aware of what was coming out of his mouth it felt so good. 

 Before long, the dark thoughts that had been swirling around his mind attempted to rekindle their fire.  

_What kind of a man lets another man stick his fingers up his ass...?_  

Something was wrong, no, _he_ was wrong to enjoy something so... deviant.  So degrading.  He felt lost.  The tears were threatening to come back.  He needed Starrick to stop or he was going to lose it.    

"Please, please, oh fuck please...you have to... stop, please God.."  Jacob's cries were getting desperate.  

Starrick complied.  He left his fingers in and started the process of stretching him out again.  A shaky sigh left Jacob's lips, and his shoulders sagged as he tried to catch his breath.  What Jacob didn't realize was that Starrick was far from done. 

Crawford pulled out the metal dilator from his robe pocket.  It looked like a smaller version of a clock weight, but with a wide top that tapered down to a smaller, rounded end.  He held it by its handle, dipped it in the olive oil, and slowly began to insert the smaller end into Jacob's ass. 

Jacob made a shocked noise and tried to pull away, only to be restrained by Starrick's free hand.  He held Jacob by his hip, pulling him back into position.  Starrick said nothing.  He only continued to push until the dilator was completely submerged and only the handle remained visible. 

Jacob could feel this..foreign object pressing against the spot that Starrick had massaged earlier.  The flush in his cheeks grew hot again, and he tried to think of something else.  Anything else.  He shifted his hips, trying to get whatever it was to move - it wouldn't budge.  

Starrick was in front of him now, studying his face.  Jacob blanched and looked down.  He couldn't meet Crawford's eyes.  He missed the knowing smile that was now creeping onto Starrick's face.  

"How are you feeling?"  Starrick's tone was almost kind.  

Jacob mumbled, "I'm fine."  Hoping Crawford wouldn't push the subject.   _God help me, just let me get through this..._  

"Hmmmm..."  Starrick nodded slowly; he took the ornate carpet beater he had been concealing behind his back and lightly struck his open hand with it. The noise of the caned beater made Jacob raise his head.  His eyes widened. 

Starrick walked around Jacob, lightly tapping Jacob's thigh with the carpet beater.  He moved around behind Jacob, rubbing small circles on his exposed butt cheek.  "Tell me the truth."  He swatted the assassin's ass with such force that it left a red swirled pattern on his skin. 

Jacob's knees buckled momentarily as he let out a surprised yelp.  "What the hell??"  That earned him another swat, this time on the other cheek.  "Starrick!  I swear to God..."  

"How are you feeling?"  Starrick repeated the question.  

"Angry as hell!"  Jacob was seething.     

_SWAT_   "How are you feeling?" 

"Jesus!  Stop!"  Jacob's cheeks were getting red again. 

_SWAT_   "How are you feeling?" 

"Stop!  Stop it!"  Jacob's voice was desperate. 

_SWAT_   "How are you feeling?"  

_Silence_  

_SWAT_   "Jacob, how are you feeling?" 

Jacob couldn't speak.  The tears that spilled out of his eyes had somehow stolen his voice away.  A choked sob escaped his lips and his cheeks flamed with the shame of it. 

"You understand now, don't you?"  Starrick moved around to face Jacob; the softness of his tone didn't match his eyes.  "The shame.  You feel it, yes?"  He raised his hand and caressed the assassin's tear-streaked face.  Jacob nodded. 

"I want to hear you say it."  Starrick's voice was commanding. 

"Y..yes,"  Jacob stammered.  "I feel ashamed."  

"Why do you feel ashamed, Jacob?"  

"Because...I liked it."  He took a deep breath.  "When... when you..." 

"Say it."  

Jacob swallowed; hot tears rolled down his face. "I can't."  

Starrick raised the cane up under Jacob's chin, raising his face to meet his.  "You liked it when I penetrated your ass with my fingers.  You liked that it was pleasurable.  You liked that it felt dirty and wrong.  You liked that you felt degraded."  Starrick searched Jacob's eyes, "Is that what you liked?" 

Listening to Starrick vocalize the fears that had been haunting him made the whole thing just that much more real.  The assassin's cheeks burned with humiliation.  

"Yes..."  Jacob swallowed and took a deep breath, his gaze meeting Starrick's. 

Crawford smiled.  "Very good."  He moved around behind Jacob again.  "You're doing very well, Jacob.  We're almost done."  Jacob hung his head, exhausted.  He didn't know how much more of this he could take.  

Suddenly, a flash of pain mixed with intense pleasure shot through Jacob's body, knocking him forward onto his toes.  Starrick had hit him with the rug beater right in the middle of his ass... hitting the metal object and forcing it up against the now swollen nodule far up inside him.  

"Did you like that, Jacob?"  Starrick's voice was taunting.  

He let out a howl, "Yes..."  He was so tired. 

Starrick hit him again in the same spot, and once more - searing pain mixed with a deep, low spike of pleasure that radiated in his belly.  He let out another sob.  

"Yes, of course you did."  _SWAT_   "Being the sexual deviant that you are..."  _SWAT_  

 It took all the willpower Jacob had to stay conscious.  His body and mind were beaten and bruised - he felt like a shell of his former self.  Another swell of pleasure hit him and he let out a low moan.  His mind swam as his erection throbbed in the air.  Starrick was calling him again.  He strained to listen. 

"You're a broken man, Jacob." _SWAT_   "You deserve this, you know."  _SWAT_   "You deserve to be punished."  _SWAT_   "Letting a man take advantage of your ass like this..."  _SWAT_   Starrick's voice was getting raspy.  

"You're loving this, aren't you?"  _SWAT_      

The assassin's voice came out a whisper, "Yes."  

"Louder!"  _SWAT_  

"Yes."  Something clicked in Jacob's brain. 

"Again!"  _SWAT_  

"Yes!"  

"Do you want to be punished?"  _SWAT_  

"Yes!"  A weight was lifting off of Jacob with each shout. 

"What are you?"  Starrick was breathing hard. 

"I'm broken!"  Jacob's cries were getting stronger.     

"What are you?"  Starrick howled, his voice was full of hunger. 

Jacob's voice became softer... and more powerful.  " I'm depraved.  I'm a deviant."  He no longer leaned on the chains that were holding him.  "I get off on pain and humiliation and I love it."  He was breathing again.  He waited for Starrick's next command, his chest heaving.  

"Who did this to you?"  Starrick's voice was low.  "Who broke you?"  Jacob could hear the anticipation in Crawford's voice.  He closed his eyes as Starrick smacked him with the cane one final time. 

"You did."  The mix of pain and pleasure was so strong now, it radiated out, filling his body.  Jacob was panting now.  He bit his lower lip as he smiled.   

When Jacob opened his eyes, Starrick was standing before him.  He shrugged off his robe and let it drop to the floor.  Starrick's muscles were tensed, his breathing was labored and he was fully erect.  Jacob stared at him with hungry eyes; his own breathing had started to quicken.  Starrick lifted his eyes and their gazes locked.  In a blink, he was on the Assassin. 

Starrick's mouth was on Jacob's, kissing him with ravenous ferocity.  His hands ran through the Assassin's hair, pulling and wrapping his fingers around the dark locks.  Jacob returned the kiss with equal intensity,  straining and pulling against his chains, his jaw working in time with his tongue.  

Jacob bit down on Starrick's lip and sucked, drawing the Grand Master's blood into his mouth.  Starrick exhaled a growl into Jacob's mouth and pulled away; licking his lips, he smirked at the proud look on Jacob's face and let his eyes drop down. 

Jacob's cock was incredibly swollen.  The leather strap had increased not only its girth, but its red tint as well.  It bobbed violently between them, smacking into Starrick's and causing intense reverberations that shot through Jacob's body.  Jacob's eyes were dark and wanting, and yet they also pleaded with Starrick to end it. 

His gaze once again met Starrick's, and the older man pulled him close.  His hand, still oiled from before, rested on Jacob's cock and squeezed it.  

Jacob yelled out, his muscles tightening from the shock.  Starrick growled his approval and began, very slowly, to run his slick hand up and down Jacob's shaft.  A low, stuttering moan escaped the Assassin as he tried to remain upright.  

Starrick placed his own erection next to Jacob's so that they stood together, their full lengths touching - and then, using both hands, he began to stroke them together.  Jacob exhaled a loud groan, still straining against his chains. 

After a moment, Starrick took away a hand and pulled Jacob's head next to his.  He breathed into the Assassin's ear.  "You've been brave enough for one night, my boy."  His voice was full of lust and pride.  "You have my permission."  And with his free hand he undid the leather strap. 

Jacob couldn't breathe.  The feeling of release overwhelmed him as the blood rushed from his groin.  His cock was tingling, shaking, as new sensations flowed through it.  Jacob gasped, trying to get air.  His chest heaved.  

"That's it," Starrick's mouth was still by his ear.  He licked, sucked and nipped at Jacob's lobe.  "Lose yourself in the sensations..."  He growled as his hands quickened their pace.  

Jacob found his voice.  He released a desperate, primal sounding yell that started and stopped with his breath.  It came and went in pitch and volume as wave after wave of pleasure built inside of him.  

"Yes, Jacob.. yes.. yes..."  Crawford's breathing started to quicken.  He bit down harder on Jacob's ear, louder growls escaping between his teeth. 

The young Assassin was all sensation.  His cries raised in pitch, sounding ever more desperate with every stroke of Starrick's hands.  He was close.  That delicious tightness in his stomach had already started working its way down. 

_Oh God..._  

"Yes, cum for me, Jacob... "  Starrick's breath was hot on Jacob's cheek.  The words flowed out of Crawford's mouth, pushing Jacob over the edge. 

With a silent scream that caught in his throat, Jacob's balls clenched and the pleasure that had been building to a fevered peak finally tipped.  His orgasm came in waves, washing over him again, and again, and again.  His cries were desperate howls until his voice broke and fell into a low roar.  Again, and again, his juices shot up and out.  It felt as if the contractions would never end. 

Starrick bit into Jacob's shoulder; his low moans grew into a loud roar, and as he fell over the edge, they evolved into heavy breaths and grunts.  His stroking slowed to a stop, and he rested his head on Jacob's shoulder. 

They stood together like that for a time, each leaning on the other and trying to catch their breaths.


	5. A Most Entertaining Evening

Starrick eventually released his grip on them, and bent to remove the dilator from Jacob's ass.  The Assassin didn't even notice when it was pulled from his body.  Crawford then unlocked the manacles around Jacob's ankles, and then one at a time, undid the ones around his wrists. 

Jacob hit the floor with a soft thud.  His hands and knees held him up for a moment, before they went out from under him.  He rolled onto his back and breathed.  A low chuckle rose up from his chest and caught between his breaths.  It turned into a loud, slow laugh - full of wonder and satisfaction. 

"Oh..my God," he laughed.  "Wow."  He smiled, his eyes opening and closing slowly.  

Jacob felt reborn.  The uneasy heaviness that he had been carrying around with him was gone.  The shame, the fear, all of it was gone.  Jacob had finally made friends with the monster under his bed.  All it took was for someone to shine a light on it. 

Another throaty laugh escaped Jacob's lips as he lay on the floor, patting his stomach.  _Ohhhhh...Mr. Starrick... You beautiful man._   He sat up, ran his fingers through his hair, and grinned. 

Starrick sat in his chair and watched Jacob roll around on the floor like a fool.  He had a curious expression on his face.  "You seem...well."  His eyes were puzzled.  

"Better than."  Jacob bounced up onto his feet and walked over to him.  "Though, I could do with a bath." 

"I'm sure."  Starrick still looked at him as if he were a lunatic.  He opened his mouth, but then closed it.  His brow furrowed. 

Jacob went to go pick up Starrick's robe.  It was on his return trip when he noticed the funny way Crawford was staring at him. 

"What?"  Jacob looked down at himself.  "It's impressive, I know... but you should know that already."  He grinned wolfishly at the confused-looking Starrick and handed the robe back. 

Crawford took the robe from Jacob's hand and, after a moment, finally found his voice. 

"How did you do it?"  

Jacob was taken aback.  "Do what?  You mean, end up like me?"  He chuckled, "That's a very big question that I'm not entirely sure I have the strength to answer."     

Starrick stood up, "No, I'm asking...  Not fifteen minutes ago you were a sobbing, shaking, shell of a man."  

"Indeed, I was."  Jacob understood where Starrick was going with this. 

"You called yourself depraved." 

"I did," Jacob agreed. 

"You said you were a deviant."  Starrick's tone was accusatory. 

"I am," he smiled proudly. 

"I degraded you.  I tortured you.  I stuck a dilator up your ass... " 

"You did."  Jacob's smile got bigger. 

He gestured to Jacob.  "And yet here you are now - no shame, no embarrassment, not even a blush in your cheek."  Starrick's look was incredulous.  

Jacob smirked and pointed at Starrick.  "You're afraid you're losing your touch."  He leaned up against a large column.  "Don't worry.  I can assure you, you're not.  I'm sure there have been many a bloke who have left your bedroom more broken than when they came in." 

Starrick lifted a finger in protest, but Jacob kept going. 

"The thing is, you _did_ break me.  Well, rather... you broke something _in_ me.  A wall, or a... a barrier or something."  He shook his head, "I'm not saying this right."  He closed his eyes and thought for a moment before continuing. 

"Earlier, you said to me, right before you started playing with my ass," Jacob grinned.  "Which was _amazing_ , by the way.  You must teach me."  He continued to talk as he pushed himself off the column and started walking towards Starrick. 

"Anyway, you said you were going to 'introduce me to my demons.'  Yes?  You remember?" 

Starrick nodded, but began to back up.  Jacob kept getting closer. 

"Well, I met my demons."  His body pushed Starrick's up against the wall.  Jacob leaned over, and breathed into his ear... "We're friends now."  

Starrick could hear the smile in Jacob's voice; it sent shivers up his spine.

 

 

Jacob felt a grand sense of satisfaction as he threw his Templar shirt into the barrel fire.  Not quite the level of satisfaction as getting into his own pants again, but it was close. 

He held the pants in his hands and smiled as fond memories of the evening flooded back to him.  

"Had it not been for you, old boy, my evening could've turned out quite differently."  He saluted the pants, "Godspeed."  And then threw them into the fire.  He thought about torching the Templar coat, but decided against it.  One never knew when an opportunity might arise where a slightly bloody Templar coat might come in handy.  

 _Who knows, I may need it to visit Mr. Starrick again._   He grinned at the thought.  Jacob laughed quietly to himself as he remembered their parting words.

 

-Flashback- 

 

Starrick was still in his dungeon when Jacob finished changing back into his borrowed clothes.  Jacob wondered if he was still leaning against the wall with that ridiculous look on his face, or had he gotten the nerve to move yet. 

 _Poor Starrick..._  

After securing his gauntlet, Jacob felt the inside of his coat pocket.  The papers will still there.  A small pang of guilt hit him in the stomach.  He wasn't overly fond of Starrick, even though they had spent an intense night of pleasurable debauchery together.  Jacob felt guilty because, well, Starrick had actually helped him.  Not that he meant to. 

"Leaving so soon?"  Starrick had his robe back on and the secret door was closing behind him. 

"I am."  Jacob smiled and strolled over to Crawford.  "It's nearly dawn - way past my bedtime."  

"I must say, I'm shocked you'd be leaving before you had, well, 'taken' your prize."  A smirk tugged at Starrick's lips.  

Jacob returned the smirk.  "Completely out of character for me, agreed."  He took a step closer, "I suppose that just means that I'll have to come back to claim it.  That is, if our agreement doesn't expire the moment I walk out that door."  He raised an eyebrow in question.  

Starrick pondered for a moment, taking a step closer to Jacob.  He looked the Assassin up and down before replying, "I believe that can be arranged."    

The electric charge that had been between them all night sparked back to life for a moment, and Jacob briefly reconsidered staying.  In a moment his sister would be proud of, he thought better of it, and went to take his leave. 

"I look forward to it."  Jacob bowed, then took Starrick's hand and brought it to his lips.  "Thank you."  He pressed his lips to Crawford's knuckles, letting them linger there.  "It's been... educational."  Jacob could almost swear there was a little more color in Starrick's cheeks than normal. 

Starrick smirked, "Indeed, it has."  He inclined his head, "Goodnight, Mr. Frye."  

"Mr. Starrick."  Jacob winked as he turned to leave.  He had made it to the door when he called over his shoulder, "I'll give your regards to Mr. Roth."  

And he was gone.

 

-End Flashback-

 

Jacob stared into the fire, his hand still stuck in his coat pocket.  He was running his fingers over the papers, hoping to find his decision in the thin edges.  Evie's voice wasn't in his head this time; it was just him.  It would have to be his choice. 

The young Assassin took the papers from his pocket, held them over the fire, and was about to drop them in when something caught his attention. 

"What have we here?"  It was a note.  

Addressed to a Mr. Jacob Frye. 

Jacob's stomach dropped as he quickly unfolded the paper. 

>   
>  _My Dear Mr. Frye,_
> 
> _I do hope this note finds you well.  You're currently unconscious on my bed as I write this, and I've not yet decided what to do with you.  I don't normally make a habit of going through my guest's things, as a general rule.  But as our night progressed, I grew more and more intrigued with your young "Mr. Christian Churchill."  And as the opportunity presented itself, my curiosity got the better of me._
> 
> _As it turned out, you almost got the better of me, as well.  I must say, I was surprised to find the notes you had taken, and even more surprised to find that charming gauntlet you had hidden by the window.  Of course, I can't let you leave with this information, I'm sure you can understand.  I've never had the pleasure of meeting an assassin before tonight.  My congratulations, Jacob - you've made a wonderful first impression._
> 
> _It's not often someone impresses me, and even less often do I give the opportunity to have the wool pulled over my eyes.  Nonetheless, you have done both.  I applaud you._
> 
> _As I said before, I've yet to decide your fate.  I do, however, have plans for you in the meantime.  I sense great things in you, Jacob.  I do hope you prove me right.  How our evening ends, I'm sure, will affect in what mood you read this letter, or if you're able to read it at all.  I hope you can.  I'd love to hear your reactions._
> 
> _It seems my time is up.  You're starting to stir, and I've yet to get you properly restrained.  You are a strong one, Mr. Frye.  This should prove to be a most entertaining evening.  I do hope we meet again._
> 
> _Yours,_
> 
> _Crawford Starrick_

 

Jacob stood there with a dumbfounded look on his face for what felt like hours.  He re-read the letter several times before finally, and begrudgingly, admitting to himself that he had been had.  His mind raced back to their parting words... 

 _"Goodnight, Mr. Frye."_  

The fire popped, breaking him out of his reverie.  

Jacob burst into laughter.  It started out slowly, with a snort.  Soon he was howling.  He choked and cackled with laughter till the stray dogs began to bark at him.  

"Well played, Mr. Starrick.  Well played."     

He was still laughing as he zipped into the early morning air and onto the neighboring rooftop.  He knew it would be a long time before he would stop.

**Notes for the Chapter:**

> Thank you all for reading! Feel free to comment - would love to hear your thoughts on it. :)
> 
> Here are some images that inspired me:  
> Tea Cart - http://www.nadeausauction.com/auctiondata/1024/images/56_1.JPG
> 
> Manacles - http://2.bp.blogspot.com/-xS4IOtmCeJ8/UpHeg1IY88I/AAAAAAAAAA4/LYL_QA-p-6k/s1600/Wrist+manacle.png
> 
> Dilator - http://wp.medicalbillingschool.org/wp-content/uploads/2013/01/rectal-dilator2.jpg
> 
> Leather Cock Strap - https://img0.etsystatic.com/057/0/10646849/il_340x270.743249944_h8id.jpg
> 
> Carpet Beater - http://www.iels.org/assets/19/A03854_l.1.jpg


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